DrugBank: Cefradine (DB01333)

targets (1) transporters (4)

Identification

Name

Cefradine

Accession Number

DB01333

Type

small molecule

Groups

approved

Description

A semi-synthetic cephalosporin antibiotic. [PubChem]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Cephradine

Brand names

Not Available

Brand name mixtures

Not Available

Categories

Anti-Bacterial Agents
Cephalosporins

CAS number

38821-53-3

Weight

Average: 349.405
Monoisotopic: 349.109626801

Chemical Formula

C₁₆H₁₉N₃O₄S

InChI Key

InChIKey=RDLPVSKMFDYCOR-UEKVPHQBSA-N

InChI

InChI=1S/C16H19N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1

Plain Text

IUPAC Name

(6R,7R)-7-[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

SMILES

[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CCC=CC1)C(O)=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Cephalosporins

Substructures

Hydroxy Compounds
Alkanes and Alkenes
Acetates
Amino Ketones
Carboxylic Acids and Derivatives
Aliphatic and Aryl Amines
Beta Lactams
Enamines
Heterocyclic compounds
Carboxamides and Derivatives
Cephalosporins
Lactams
Azetidines

Pharmacology

Indication

Not Available

Pharmacodynamics

Not Available

Mechanism of action

Cefradine is a first generation cephalosporin antibiotic with a spectrum of activity similar to Cefalexin. Cefradine, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Cefradine interferes with an autolysin inhibitor.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Route of elimination

Over 90 percent of the drug is excreted unchanged in the urine within six hours.

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Not Available

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Glaxosmithkline
Barr laboratories inc
Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Teva pharmaceuticals usa inc
Vitarine pharmaceuticals inc
Apothecon inc div bristol myers squibb
Ersana inc sub er squibb and sons
Bristol myers squibb co

Packagers

E.R. Squibb and Sons LLC
H.J. Harkins Co. Inc.
Major Pharmaceuticals
PD-Rx Pharmaceuticals Inc.
Pharmedix
Prepackage Specialists
Prescription Dispensing Service Inc.
Teva Pharmaceutical Industries Ltd.

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

140 oC

Experimental Properties

Property	Value	Source
water solubility	21.3 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp

Predicted Properties

Property	Value	Source
water solubility	7.78e-01 g/l	ALOGPS
logP	0.70	ALOGPS
logP	-3.93	ChemAxon Molconvert
logS	-2.65	ALOGPS
pKa	11.99	ChemAxon Molconvert
hydrogen acceptor count	5	ChemAxon Molconvert
hydrogen donor count	3	ChemAxon Molconvert
polar surface area	112.73	ChemAxon Molconvert
rotatable bond count	4	ChemAxon Molconvert
refractivity	92.00	ChemAxon Molconvert
polarizability	33.19	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Neiss ES: Cephradine—a summary of preclinical studies and clinical pharmacology. J Ir Med Assoc. 1973 Mar 24;Suppl:1-12. Pubmed

External Links

Resource	Link
KEGG Drug	D00264
KEGG Compound	C06897
PubChem Compound	38103
PubChem Substance	46505082
ChemSpider	34933
ChEBI	3547
ChEMBL	3547
Therapeutic Targets Database	DAP000454
Drug Product Database	0
Wikipedia	http://en.wikipedia.org/wiki/Cefradine

ATC Codes

J01DB09

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Penicillin-binding protein 1A Pharmacological action: yes Actions: inhibitor Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits) Organism class: bacterial UniProt ID: P02918 Gene: mrcA Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Sharma UK, Dwarakanath P, Banerjee N, Town C, Balganesh TS: Expression and characterization of the ponA (ORF I) gene of Haemophilus influenzae: functional complementation in a heterologous system. J Bacteriol. 1995 Dec;177(23):6745-50. Pubmed

Targets

1. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)

Organism class: bacterial
UniProt ID: P02918 Link_out

Gene: mrcA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Sharma UK, Dwarakanath P, Banerjee N, Town C, Balganesh TS: Expression and characterization of the ponA (ORF I) gene of Haemophilus influenzae: functional complementation in a heterologous system. J Bacteriol. 1995 Dec;177(23):6745-50. Pubmed

Transporters
1. Organic cation/carnitine transporter 2 Actions: inhibitor Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3 UniProt ID: O76082 Gene: SLC22A5 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. Pubmed 2. Oligopeptide transporter, small intestine isoform Actions: substrate, inhibitor Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products UniProt ID: P46059 Gene: SLC15A1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadee W, Amidon GL: 5’-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res. 1998 Aug;15(8):1154-9. Pubmed Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. Pubmed Saito H, Okuda M, Terada T, Sasaki S, Inui K: Cloning and characterization of a rat H+/peptide cotransporter mediating absorption of beta-lactam antibiotics in the intestine and kidney. J Pharmacol Exp Ther. 1995 Dec;275(3):1631-7. Pubmed Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed Terada T, Saito H, Mukai M, Inui K: Characterization of stably transfected kidney epithelial cell line expressing rat H+/peptide cotransporter PEPT1: localization of PEPT1 and transport of beta-lactam antibiotics. J Pharmacol Exp Ther. 1997 Jun;281(3):1415-21. Pubmed 3. Oligopeptide transporter, kidney isoform Actions: inhibitor Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides UniProt ID: Q16348 Gene: SLC15A2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed 4. Solute carrier family 22 member 6 Actions: inhibitor UniProt ID: Q4U2R8 Gene: hROAT1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. Pubmed

Transporters

1. Organic cation/carnitine transporter 2

Actions: inhibitor

Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3

UniProt ID: O76082 Link_out

Gene: SLC22A5 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. Pubmed

2. Oligopeptide transporter, small intestine isoform

Actions: substrate, inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products

UniProt ID: P46059 Link_out

Gene: SLC15A1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadee W, Amidon GL: 5’-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res. 1998 Aug;15(8):1154-9. Pubmed
Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. Pubmed
Saito H, Okuda M, Terada T, Sasaki S, Inui K: Cloning and characterization of a rat H+/peptide cotransporter mediating absorption of beta-lactam antibiotics in the intestine and kidney. J Pharmacol Exp Ther. 1995 Dec;275(3):1631-7. Pubmed
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed
Terada T, Saito H, Mukai M, Inui K: Characterization of stably transfected kidney epithelial cell line expressing rat H+/peptide cotransporter PEPT1: localization of PEPT1 and transport of beta-lactam antibiotics. J Pharmacol Exp Ther. 1997 Jun;281(3):1415-21. Pubmed

3. Oligopeptide transporter, kidney isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides

UniProt ID: Q16348 Link_out

Gene: SLC15A2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed

4. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out

Gene: hROAT1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. Pubmed

Comments

Drug created on June 30, 2007 12:05 / Updated on April 19, 2011 15:10

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.